Over the recent period, there has been an increasing interest in the use of pulsed infrared thermography (PT) for the non-destructive evaluation of Cultural Heritage (CH). Unlike other techniques that are commonly employed in the same field, PT enables the depth-resolved detection of different kinds of subsurface features, thus providing helpful information for both scholars and restorers. Due to this reason, several research activities are currently underway to further improve the PT effectiveness. In this manuscript, the specific use of PT for the analysis of three different types of CH, namely documentary materials, panel paintings–marquetery, and mosaics, will be reviewed. In the latter case, i.e., mosaics, passive thermography combined with ground penetrating radar (GPR) and digital microscopy (DM) have also been deepened, considering their suitability in the open field. Such items have been selected because they are characterized by quite distinct physical and structural properties and, therefore, different PT (and, in some cases, verification) approaches have been employed for their investigations.